10 Date Night Approved Men's Valentine's Day Dress Shirts (2024)

No matter how you celebrate this romantic holiday, I’ve rounded up some excellent options for men’s Valentine shirts right here.

Did you know that in third-century Rome, Emperor Claudius banned soldiers from getting married? He didn’t want them to have anything to live for.

So dark.

Ever the advocate for love, Saint Valentine, a priest at the time, officiated underground marriage ceremonies (I smell an Oscar-bait period piece).

So there you go. Valentine’s Day wasn’t just made up by greeting card companies. Well, not completely, at least. What they did likely do, though, is curate the romantic color palette we often associate with the holiday.

When looking for men’s Valentine’s shirts, reds, pinks, and deep shades are good colors to level up your regular date night attire. However, I know that not everyone likes these hues. And I know not everyone celebrates V-Day the same way.

The men’s Valentine’s Day dress shirts rounded up here, though mostly traditional, keep all of this in mind.

Quick Take

Here are our recommendations from the list:

Read on for more info and the complete list…

Men’s Valentines Day Shirts

Here they are, in no particular order!

Mizzen and Main Ellis Oxford in True Pink

The Ellis Oxford from Mizzen and Main is a pink shirt for men who don’t wear pink shirts. The hue is so light and neutral it would look good with anything. Wear it with dress pants on a formal date or with chinos on a more casual one.

Part of this has to do with the fact the design is so simple and perfectly balanced. It has the clean lines and minimalist composition of a formal dress shirt. However, the button-down collar gives it a touch of brawn that allows you to wear it with or without a tie.

Suitsupply Red Slim Fit Shirt

Not only does Suitsupply provide good custom-made suits, but they also have some great immediately shoppable (i.e. off-the-rack) shirts as well.

This slim fit number in red is a traditional dress shirt, but one constructed in light linen. It makes the color a little less intense — still striking but not intimidating.

Moreover, it has a silk-like luxuriousness on top of being highly breathable. You can definitely pull this shirt off all year long.

This Italian-woven garment is definitely dressier than the Mizzen and Main Ellis, but the spread collar is curved, so you can also wear it with or without a tie.

Luca Faloni Red Brushed Cotton Shirt

This handmade Italian brushed cotton shirt from Luca Faloni has an effortless yet luxe aesthetic. Brushed cotton is extra breathable with a fleece-like texture that combines coziness with elegance.

The satiny texture is complemented by stately mother-of-pearl buttons and a paramontura collar.

“Paramontura” means that the collar is made with one piece of cloth that travels down to the front, creating a placket. This ensures the collar keeps its shape and structure throughout the night.

Ash & Erie Everyday Shirt in Burgundy

The concept behind is right up our alley since they’re dedicated to giving us shorter gents well-fitting clothes. And, they’ve got an excellent brushed flannel button-down, the Everyday Shirt, in the Valentine’s-appropriate shade of burgundy.

You can go for the heather burgundy for a softer look that would pair beautifully with linen pants or chinos. Otherwise, there’s the Houndstooth burgundy, which has a more solid visual pattern that goes naturally with either a sports coat or jeans.

It’s a more casual button-up but is still classy without being stuffy.

Mizzen and Main Leeward Dress Shirt in Plum Dot Print

The Mizzen and Main Leeward Dress Shirt is a touch more fashion-forward, though I wouldn’t call it loud by any means. The dot print is fun, though the dark plum hue brings the design down to earth, ensuring it isn’t overly dandy.

The best part about this shirt is how secretly functional and practical it is. It’s made from performance materials, including spandex for stretch and polyester for durability. This also means it’s quick-drying and wrinkle-free.

Even more, the collar points feature a button-down design, but one in which the buttons sit behind the points. This keeps the collar in place while maintaining its formal look.

Just keep in mind that you shouldn’t iron a performance shirt. It’s unlikely this guy will get wrinkled, but if it does, use a steamer or hang it in the bathroom while you take a hot shower.

State & Liberty Weston Shirt in Light Blue With Subtle Pink Accents

State & Liberty also makes four-way stretch athletic shirts using the magic of polyester and spandex. What I love about the Weston specifically is that it looks like a light blue plaid shirt with a bit of warmth that you can’t quite place your finger on.

What it is is that the black-lined pattern has a subtle pink glow to it, perfect for Valentine’s Day and perfect for guys who aren’t comfortable wearing pink. This shirt moves away from the traditional shades of red, but not completely.

It would actually pair excellently with accessories, like a tie or pocket square, in any shade of red because of the subtle pink accents.

Paul Fredrick White Shirt With Red Accents

This white shirt from Paul Fredrick is a by-the-books traditional Oxford shirt. It has a classic fit and a split yoke, which I think gives it a cleaner look overall.

What makes this two-ply cotton shirt special is all of the red accents. The buttons are red, as are the interiors of the collar and cuffs.

So, you can choose just how much red you want to flash.

With a tie, the entire shirt would be understated with red buttons that peak out occasionally.

With the top buttons undone, you’d have a more prominent accent via the collar interior. And on a super casual date, you can even neatly fold your sleeves up to expose the red interior on each arm.

Ash & Erie Classic Dress Shirt

And, of course, if you want to go for a classic white or light blue dress shirt, there’s absolutely nothing wrong with that. You don’t always have to dress on theme, as long as you’re sporting clean lines and a good fit.

is a wrinkle-resistant semi-spread with a highly formal French cuff. This means you can wear it with a full suit or use it to level up a casual combination.

Ted Baker Stitched Polo

If your Valentine’s date is on the casual side, say a relaxed dinner at home, you can still incorporate class and a sense that you’re acknowledging the holiday.

The geometric pattern on this stitched polo from Ted Baker is classic, like something a dapper gent would wear to a weekend barbecue in the ‘50s when men wore suits to the airport.

It’s still relaxed, but sophisticated and with a nice Valentine’s-appropriate color palette to boot.

The Resort Co Terry Popover Shirt

The Resort Co is a great brand to turn to if you’re spending Valentine’s Day on a tropical vacation. As someone who lives somewhere with a very cold February, I don’t blame you if that’s what you want to do.

Though vacations are generally casual affairs, you still want to avoid being sloppy in a Valentine’s Day situation. This Terry Popover Shirt has a similar silhouette to a vintage rugby shirt, giving it structure.

However, the soft terry fabric and cutaway collar bring a balance of formality and casualness. Wear this shirt with trousers, driving loafers, and even a blazer if there’s a slight breeze on that island.

FAQs

Still, have questions about what to wear on Valentine’s Day? Here are some answers!

What Shirt Is Good To Wear on Valentine’s Day?

You’ll want to go for a dress shirt or at least a clean-lined casual shirt if you’re on a more relaxed date. Just make sure you’re leveling up what you’d wear on any other date since it’s a special occasion.

What Colors Should You Wear on Valentine’s Day?

Common colors to wear on Valentine’s Day include shades of red, such as burgundy and light pink. However, you can go for any deep, formal colors as well.

How Do I Choose a Dress Shirt for a Guy?

Just make sure you’re choosing a proper dress shirt for the occasion. Go for French cuffs and classic collars for more formal occasions and button-down collars for more casual ones. Either way, it should be well-fitted with a clean silhouette.

Conclusion: A Shirt for Every Kind of Valentine’s Day

Again, you don’t have to dress to the color theme if that isn’t your personal style. But it’s still important, especially if you’re on a date, to acknowledge the specialness of the day.

By simply dressing up a bit, you’ve already made the first step in doing that.

How do you celebrate Valentine’s Day? Do you dress more casually or formally? Sound off in the comments!